organic compounds
(E)-4-Nitro-2-[(phenylimino)methyl]phenol
aCentre for Advanced Material Research, Government Arts College (Autonomous), Kumbakonam 612 001, Tamilnadu, India, bPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, and cPG Department of Physics, A.D.M. College for Women (Autonomous), Nagapattinam 611 001, Tamilnadu, India
*Correspondence e-mail: thiruvalluvar.a@gmail.com
In the title compound, C13H10N2O3, the dihedral angle between the planes of the two aryl rings is 7.42 (10)°. An intramolecular O—H⋯N hydrogen bond generates an S(6) ring. The features C—H⋯O hydrogen bonds.
CCDC reference: 1508947
Structure description
We report here the synthesis and characterization of the title Schiff base derivative (Fig. 1)) prepared from the condensation reaction of an equimolar proportion of 5-nitrosalicylaldehyde and aniline in CCl4. The diversified nature of salicylaldehyde derivatives containing as an integral part of the structure exhibit a variety of important biological properties, including anti-bacterial, anti-cancer and anti-tumor activities (Ida Malarselvi et al., 2016).
The benzene and phenyl rings are inclined at 7.42 (10)° to one another. The molecule has an E conformation about the C=N bond, and the C5—C7=N2—C8 torsion angle is −177.03 (16)°. The 4-nitro group is slightly tilted away from the benzene ring to which it is attached [O1—N1—C1—C2 = −5.8 (3)° and O2—N1—C1—C6 = −2.7 (3)°]. The strong intramolecular O3—H3A⋯N2 hydrogen bond (N⋯H distance of 1.83 Å) generates an S(6) ring. The strong band in the IR at 1632 cm−1 is assigned to the C7=N2 stretching frequency of the imine group of Schiff base with the C7=N2 bond distance of 1.276 (2) Å indicative of double-bond character. The features C2—H2⋯O1 and C7—H7⋯O2 hydrogen bonds (Table 1, Fig. 2).
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Yan et al., (2014) have reported the of 4-bromo-2-[(phenylimino)methyl]phenol, in which the molecule is essentially planar (r.m.s. deviation = 0.026 Å).
Synthesis and crystallization
0.2 g (0.001 mol) of 5-nitrosalicylaldehyde was dissolved in 5 ml of CCl4. To this solution, 0.1 g (0.111 mol) of aniline was added dropwise with constant stirring for 1 h. During this time, the solution turned deep yellow. On standing for two weeks with slow evaporation of the solvent, yellow crystals of the title compound were obtained.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1508947
https://doi.org/10.1107/S2414314616015959/hg4016sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616015959/hg4016Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616015959/hg4016Isup3.cdx
Supporting information file. DOI: https://doi.org/10.1107/S2414314616015959/hg4016Isup4.cml
Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).C13H10N2O3 | F(000) = 504 |
Mr = 242.23 | Dx = 1.412 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0774 (10) Å | Cell parameters from 3323 reflections |
b = 6.5801 (6) Å | θ = 4.0–24.5° |
c = 21.668 (3) Å | µ = 0.10 mm−1 |
β = 98.240 (5)° | T = 296 K |
V = 1139.8 (2) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.25 × 0.20 mm |
Bruker Kappa APEXII CCD diffractometer | 1645 reflections with I > 2σ(I) |
Radiation source: Sealed tube | Rint = 0.029 |
ω and φ scan | θmax = 28.4°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −10→9 |
Tmin = 0.95, Tmax = 0.96 | k = −8→8 |
15249 measured reflections | l = −28→28 |
2857 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.0473P)2 + 0.3112P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2857 reflections | Δρmax = 0.17 e Å−3 |
164 parameters | Δρmin = −0.22 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.2784 (2) | 0.1044 (3) | −0.11963 (7) | 0.0468 (4) | |
C2 | 0.1930 (3) | 0.2130 (3) | −0.16876 (8) | 0.0563 (5) | |
H2 | 0.179342 | 0.159614 | −0.208907 | 0.068* | |
C3 | 0.1293 (3) | 0.3986 (3) | −0.15790 (8) | 0.0608 (5) | |
H3 | 0.072527 | 0.472297 | −0.190992 | 0.073* | |
C4 | 0.1474 (2) | 0.4797 (3) | −0.09835 (8) | 0.0508 (5) | |
C5 | 0.2374 (2) | 0.3697 (3) | −0.04848 (7) | 0.0450 (4) | |
C6 | 0.3016 (2) | 0.1809 (3) | −0.06025 (7) | 0.0464 (4) | |
H6 | 0.360524 | 0.106126 | −0.027877 | 0.056* | |
C7 | 0.2662 (2) | 0.4542 (3) | 0.01343 (8) | 0.0506 (5) | |
H7 | 0.323271 | 0.377170 | 0.045658 | 0.061* | |
C8 | 0.2495 (2) | 0.7204 (3) | 0.08524 (8) | 0.0464 (4) | |
C9 | 0.3526 (2) | 0.6347 (3) | 0.13497 (8) | 0.0565 (5) | |
H9 | 0.403539 | 0.509943 | 0.130314 | 0.068* | |
C10 | 0.3796 (3) | 0.7343 (3) | 0.19118 (9) | 0.0643 (6) | |
H10 | 0.449407 | 0.677035 | 0.224503 | 0.077* | |
C11 | 0.3043 (3) | 0.9175 (4) | 0.19849 (10) | 0.0705 (6) | |
H11 | 0.322110 | 0.983561 | 0.236820 | 0.085* | |
C12 | 0.2030 (3) | 1.0033 (3) | 0.14949 (10) | 0.0696 (6) | |
H12 | 0.151911 | 1.127794 | 0.154403 | 0.083* | |
C13 | 0.1768 (2) | 0.9057 (3) | 0.09319 (9) | 0.0567 (5) | |
H13 | 0.108938 | 0.965574 | 0.059827 | 0.068* | |
N1 | 0.3522 (2) | −0.0902 (2) | −0.13139 (7) | 0.0586 (4) | |
N2 | 0.21561 (19) | 0.6317 (2) | 0.02536 (6) | 0.0486 (4) | |
O1 | 0.3253 (2) | −0.1609 (2) | −0.18406 (7) | 0.0843 (5) | |
O2 | 0.4381 (2) | −0.1762 (2) | −0.08827 (7) | 0.0723 (5) | |
O3 | 0.08189 (19) | 0.6599 (2) | −0.08898 (6) | 0.0665 (4) | |
H3A | 0.106727 | 0.692303 | −0.052274 | 0.100* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0517 (11) | 0.0475 (10) | 0.0416 (9) | −0.0074 (8) | 0.0083 (8) | 0.0025 (7) |
C2 | 0.0634 (13) | 0.0679 (13) | 0.0357 (9) | −0.0131 (10) | 0.0005 (8) | 0.0027 (8) |
C3 | 0.0643 (13) | 0.0672 (13) | 0.0456 (10) | −0.0038 (10) | −0.0102 (9) | 0.0162 (9) |
C4 | 0.0474 (11) | 0.0519 (11) | 0.0518 (10) | −0.0024 (9) | 0.0028 (8) | 0.0111 (8) |
C5 | 0.0453 (10) | 0.0492 (10) | 0.0396 (9) | −0.0041 (8) | 0.0027 (7) | 0.0052 (7) |
C6 | 0.0494 (11) | 0.0506 (10) | 0.0378 (9) | −0.0009 (8) | 0.0009 (7) | 0.0072 (7) |
C7 | 0.0540 (12) | 0.0545 (11) | 0.0422 (9) | 0.0021 (9) | 0.0032 (8) | 0.0063 (8) |
C8 | 0.0416 (10) | 0.0518 (10) | 0.0465 (9) | −0.0046 (8) | 0.0091 (8) | 0.0000 (8) |
C9 | 0.0554 (12) | 0.0619 (12) | 0.0525 (11) | 0.0060 (9) | 0.0087 (9) | −0.0016 (9) |
C10 | 0.0556 (13) | 0.0841 (15) | 0.0515 (11) | 0.0048 (11) | 0.0018 (9) | −0.0030 (10) |
C11 | 0.0585 (14) | 0.0892 (16) | 0.0627 (13) | −0.0009 (12) | 0.0048 (10) | −0.0242 (11) |
C12 | 0.0649 (15) | 0.0666 (13) | 0.0758 (14) | 0.0072 (11) | 0.0056 (11) | −0.0184 (11) |
C13 | 0.0511 (12) | 0.0586 (12) | 0.0590 (11) | 0.0041 (9) | 0.0029 (9) | −0.0009 (9) |
N1 | 0.0688 (12) | 0.0590 (10) | 0.0495 (9) | −0.0078 (9) | 0.0134 (8) | −0.0047 (8) |
N2 | 0.0477 (9) | 0.0506 (9) | 0.0483 (8) | −0.0002 (7) | 0.0091 (7) | 0.0006 (7) |
O1 | 0.1271 (16) | 0.0753 (10) | 0.0519 (8) | −0.0080 (9) | 0.0177 (9) | −0.0165 (7) |
O2 | 0.0777 (11) | 0.0665 (9) | 0.0702 (10) | 0.0142 (8) | 0.0022 (8) | −0.0039 (7) |
O3 | 0.0689 (10) | 0.0614 (9) | 0.0662 (9) | 0.0136 (7) | −0.0008 (7) | 0.0115 (7) |
C1—C6 | 1.369 (2) | C8—C9 | 1.384 (2) |
C1—C2 | 1.382 (2) | C8—N2 | 1.413 (2) |
C1—N1 | 1.450 (2) | C9—C10 | 1.373 (3) |
C2—C3 | 1.359 (3) | C9—H9 | 0.9300 |
C2—H2 | 0.9300 | C10—C11 | 1.370 (3) |
C3—C4 | 1.385 (3) | C10—H10 | 0.9300 |
C3—H3 | 0.9300 | C11—C12 | 1.366 (3) |
C4—O3 | 1.326 (2) | C11—H11 | 0.9300 |
C4—C5 | 1.412 (2) | C12—C13 | 1.368 (3) |
C5—C6 | 1.384 (2) | C12—H12 | 0.9300 |
C5—C7 | 1.440 (2) | C13—H13 | 0.9300 |
C6—H6 | 0.9300 | N1—O2 | 1.220 (2) |
C7—N2 | 1.276 (2) | N1—O1 | 1.2228 (19) |
C7—H7 | 0.9300 | O3—H3A | 0.8200 |
C8—C13 | 1.375 (3) | ||
C6—C1—C2 | 121.32 (17) | C13—C8—N2 | 116.85 (16) |
C6—C1—N1 | 119.04 (15) | C9—C8—N2 | 124.19 (16) |
C2—C1—N1 | 119.58 (16) | C10—C9—C8 | 119.81 (19) |
C3—C2—C1 | 119.42 (17) | C10—C9—H9 | 120.1 |
C3—C2—H2 | 120.3 | C8—C9—H9 | 120.1 |
C1—C2—H2 | 120.3 | C11—C10—C9 | 120.4 (2) |
C2—C3—C4 | 121.04 (17) | C11—C10—H10 | 119.8 |
C2—C3—H3 | 119.5 | C9—C10—H10 | 119.8 |
C4—C3—H3 | 119.5 | C12—C11—C10 | 120.01 (19) |
O3—C4—C3 | 119.74 (16) | C12—C11—H11 | 120.0 |
O3—C4—C5 | 120.94 (16) | C10—C11—H11 | 120.0 |
C3—C4—C5 | 119.31 (17) | C11—C12—C13 | 119.9 (2) |
C6—C5—C4 | 118.98 (15) | C11—C12—H12 | 120.1 |
C6—C5—C7 | 120.24 (15) | C13—C12—H12 | 120.1 |
C4—C5—C7 | 120.76 (16) | C12—C13—C8 | 120.93 (19) |
C1—C6—C5 | 119.92 (16) | C12—C13—H13 | 119.5 |
C1—C6—H6 | 120.0 | C8—C13—H13 | 119.5 |
C5—C6—H6 | 120.0 | O2—N1—O1 | 122.93 (18) |
N2—C7—C5 | 121.91 (16) | O2—N1—C1 | 118.55 (15) |
N2—C7—H7 | 119.0 | O1—N1—C1 | 118.52 (17) |
C5—C7—H7 | 119.0 | C7—N2—C8 | 122.60 (15) |
C13—C8—C9 | 118.95 (17) | C4—O3—H3A | 109.5 |
C6—C1—C2—C3 | −0.7 (3) | C13—C8—C9—C10 | 0.5 (3) |
N1—C1—C2—C3 | −177.65 (18) | N2—C8—C9—C10 | 179.08 (18) |
C1—C2—C3—C4 | −0.5 (3) | C8—C9—C10—C11 | 0.4 (3) |
C2—C3—C4—O3 | −179.07 (19) | C9—C10—C11—C12 | −0.7 (3) |
C2—C3—C4—C5 | 1.6 (3) | C10—C11—C12—C13 | 0.1 (3) |
O3—C4—C5—C6 | 179.13 (17) | C11—C12—C13—C8 | 0.8 (3) |
C3—C4—C5—C6 | −1.6 (3) | C9—C8—C13—C12 | −1.1 (3) |
O3—C4—C5—C7 | −2.6 (3) | N2—C8—C13—C12 | −179.80 (18) |
C3—C4—C5—C7 | 176.72 (17) | C6—C1—N1—O2 | −2.7 (3) |
C2—C1—C6—C5 | 0.7 (3) | C2—C1—N1—O2 | 174.36 (17) |
N1—C1—C6—C5 | 177.68 (16) | C6—C1—N1—O1 | 177.16 (17) |
C4—C5—C6—C1 | 0.4 (3) | C2—C1—N1—O1 | −5.8 (3) |
C7—C5—C6—C1 | −177.87 (16) | C5—C7—N2—C8 | −177.03 (16) |
C6—C5—C7—N2 | 176.63 (17) | C13—C8—N2—C7 | −174.99 (17) |
C4—C5—C7—N2 | −1.7 (3) | C9—C8—N2—C7 | 6.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.93 | 2.60 | 3.278 (2) | 130 |
C7—H7···O2ii | 0.93 | 2.41 | 3.252 (2) | 150 |
O3—H3A···N2 | 0.82 | 1.83 | 2.5637 (19) | 149 |
Symmetry codes: (i) −x+1/2, y+1/2, −z−1/2; (ii) −x+1, −y, −z. |
Acknowledgements
The authors would like to acknowledge the University Grants Commission (UGC), New Delhi, for providing funds under Minor Research Project Scheme No. FERP5150/14 (SERO/UGC). The authors are grateful to the Sophisticated Analytical Instrument Facility (SAIF), IITM, Chennai 600 036, Tamilnadu, India, for the single-crystal X-ray diffraction data.
References
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